tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate

Base Information

• Chemical Name: tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate
• CAS No.: 676241-16-0
• Molecular Formula: C₃₂H₃₇N₃O₆
• Molecular Weight: 559.662
• Mol file: 676241-16-0.mol

Synonyms:tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate

Chemical Property of tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate

There total 5 articles about tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

tert-butyl alcohol (75-65-0) + ((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (676241-15-9) → tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate (676241-16-0)

Guidance literature:

With acetic anhydride; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester (676241-01-3) → tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate (676241-16-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium methylate / methanol / 20 h / 20 °C

2.1: triethylamine / dichloromethane / 20 h / 20 °C

3.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

4.1: ozone / dichloromethane / 0.5 h / -78 °C

4.2: NaBH₄ / 11; 15 / 20 h / 20 °C

5.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

With sodium azide; sodium methylate; acetic anhydride; ozone; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Zemplen deacetylation;

DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol (676241-03-5) → tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-D-gulo-hepturonate (676241-16-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 20 h / 20 °C

2.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

3.1: ozone / dichloromethane / 0.5 h / -78 °C

3.2: NaBH₄ / 11; 15 / 20 h / 20 °C

4.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

With sodium azide; acetic anhydride; ozone; triethylamine; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2003.12.032

upstream raw materials:

tert-butyl alcohol

((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

(2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

(2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

(2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

(2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid